Potassium Phosphate, Tribasic → HCID 178518664, compound

HRID 388137Notes

Reaction equation

HRID 388137 reaction equation
[O:1]=[C:2]1[NH:18][C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)[N:9]=[C:4]2[N:3]1[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.BrC1N=C2N(CCN3CCCCC3)C(=O)[NH:36][C:31]2=[N:30]C=1.C(C1C=CC(B(O)O)=CC=1)#N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[N:30]1[N:15]=[C:14]([C:13]2[CH:12]=[CH:11][C:10]([C:8]3[N:9]=[C:4]4[N:3]([CH2:19][CH2:20][N:21]5[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]5)[C:2](=[O:1])[NH:18][C:5]4=[N:6][CH:7]=3)=[CH:17][CH:16]=2)[NH:36][CH:31]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27343264-Cyanophenylboronic acidHCID 66699762HCID 66699762, compoundHCID 86626414HCID 86626414, compound

Product 1

HCID 178518664HCID 178518664, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(2-Oxo-3-(2-(piperidin-1-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzonitrile. 6-Bromo-1-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (1.2 g., 3.68 mmol), 4-cyanophenylboronic acid (0.595 g., 4.05 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.3 g., 0.368 mmol) and potassium phosphate (3.12 g., 14.7 mmol) were combined in DMF (9 mL) and heated in a sealed tube to 100° C. overnight. The flask was cooled to rt and the reaction mixture was filtered through celite, washed with methanol and ethyl acetate. The filtrate and washes were combined, concentrated and treated with water. The product was extracted into ethyl acetate, the organic layer was concentrated and the resulting material was subjected to silica gel chromatography (60-100% ethyl acetate in hexanes) to yield the title compound (0.5 g., 39% yield). MS (ESI) m/z 349.3[M+1]+.

Workup

  1. temperatureThe flask was cooled to rt
  2. filtrationthe reaction mixture was filtered through celite
  3. washwashed with methanol and ethyl acetate
  4. concentrationconcentrated
  5. additiontreated with water
  6. extractionThe product was extracted into ethyl acetate
  7. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-b790a11b96c244e9af7bf6b6bbd3a22a
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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